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5'-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate

Product Name5'-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate
CAS3031-94-5
MFC9H15N4O8P
MW338.21
EINECS221-212-1
MOL File3031-94-5.mol

Chemical Properties

Melting point	198-202°C dec.
Boiling point	845.3±75.0 °C(Predicted)
Density	2.30±0.1 g/cm3(Predicted)
storage temp.	-20°C
solubility	DMSO (Slightly, Heated, Sonicated), Methanol (Slightly), Water (Slightly)
pka	1.86±0.10(Predicted)
form	White to light pink solid
color	White to Pink
optical activity	[α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate
Water Solubility	water: 1mg/mL DMSO: 30mg/mL
Stability	Hygroscopic
InChI	1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChIKey	UDYDDOATBNVEES-UUOKFMHZSA-N
SMILES	O[C@H]1[C@@H](O)[C@H](N2C=NC(C(N)=O)=C2N)O[C@@H]1COP(O)(O)=O

Safety Information

Safety Statements	24/25
WGK Germany	3
HS Code	29349990
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

White Powder With Pink Tinge.

Uses

AICAR monophosphate is a 5′′-phosphorylated analog of cell permeable AICAR that mimics AMP. AICAR is an adenosine monophophate (AMP)-activated protein kinase (AMPK) activator/agonist.

Definition

ChEBI: AICA ribonucleotide is a 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative. It has a role as a cardiovascular drug, a plant metabolite, a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is a 1-(phosphoribosyl)imidazolecarboxamide and an aminoimidazole. It is functionally related to an acadesine. It is a conjugate acid of a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2-).

General Description

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate (AICAR monophosphate) is an intermediate metabolite in the purine de novo synthesis pathway and a potent activator of the human AMP-activated protein kinase (AMPK) activity in vitro. It can play an important regulatory role.

Biochem/physiol Actions

A 5′-phosphorylated analog of cell permeable AICAR that mimics adenosine monophosphate (AMP). It is an AMP-activated protein kinase (AMPK) activator.In humans, 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate (AICAR) is found to be accumulated in numerous metabolic diseases. It can increase the endurance of sedentary mice. AICAR exhibits antiproliferative effects. It can induce apoptosis of aneuploid cells.

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